US5498701A - Basic disazo compounds containing sulphonic acid groups - Google Patents

Basic disazo compounds containing sulphonic acid groups Download PDF

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Publication number
US5498701A
US5498701A US08/363,672 US36367294A US5498701A US 5498701 A US5498701 A US 5498701A US 36367294 A US36367294 A US 36367294A US 5498701 A US5498701 A US 5498701A
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alkyl
independently
methyl
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formula
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Reinhard Pedrazzi
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Clariant Finance BVI Ltd
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Sandoz AG
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Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/02—Material containing basic nitrogen
    • D06P3/04—Material containing basic nitrogen containing amide groups
    • D06P3/32—Material containing basic nitrogen containing amide groups leather skins
    • D06P3/3206—Material containing basic nitrogen containing amide groups leather skins using acid dyes
    • D06P3/3226—Material containing basic nitrogen containing amide groups leather skins using acid dyes dis-polyazo
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
    • C09B35/02—Disazo dyes
    • C09B35/021—Disazo dyes characterised by two coupling components of the same type
    • C09B35/027—Disazo dyes characterised by two coupling components of the same type in which the coupling component is a hydroxy-amino compound
    • C09B35/029—Amino naphthol
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
    • C09B35/02—Disazo dyes
    • C09B35/039—Disazo dyes characterised by the tetrazo component
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B43/00—Preparation of azo dyes from other azo compounds
    • C09B43/12—Preparation of azo dyes from other azo compounds by acylation of amino groups
    • C09B43/136—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents
    • C09B43/16—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents linking amino-azo or cyanuric acid residues
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B43/00—Preparation of azo dyes from other azo compounds
    • C09B43/40—Preparation of azo dyes from other azo compounds by substituting hetero atoms by radicals containing other hetero atoms
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/58—Material containing hydroxyl groups
    • D06P3/60—Natural or regenerated cellulose
    • D06P3/6008—Natural or regenerated cellulose using acid dyes
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
    • D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
    • D21H21/28—Colorants ; Pigments or opacifying agents
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/916—Natural fiber dyeing
    • Y10S8/919—Paper

Definitions

  • the invention relates to basic sulpho group-containing disazo compounds which are metal-free, and their salts and to a process for the preparation and their use as dyestuffs as well as dyeing preparations thereof.
  • each of R 1 to R 4 is independently hydrogen, halogen, hydroxy, C 1-4 alkyl, C 1-4 alkoxy, --NHCOC 1-4 alkyl or --NHCONH 2 ,
  • each of X 1 to X 4 is independently an aliphatic, cycloaliphatic or heterocyclic amino group containing at least two nitrogen atoms, with the proviso that each of these amino groups bears a protonatable nitrogen atom or quaternary ammonium ion, and at least one of these amino groups bears a primary amino group, and
  • X 5 is an aliphatic, cycloaliphatic or heterocyclic amino group containing at least two nitrogen atoms one of which is a protonatable nitrogen atom or quaternary ammonium ion, or an aromatic diamino group of which the terminal amino group is substituted by ##STR3## in which each X 6 and X 7 is independently an aliphatic, cycloaliphatic or heterocyclic amino group which contains at least two nitrogen atoms one of which is a protonatable nitrogen atom or a quaternary ammonium ion,
  • the number of X 1 to X 5 containing a primary amino group is preferably 2 to 4; more preferably, X 5 does not contain a primary amino group.
  • each R 1 and R 3 is preferably R 1a and R 3a , where each R 1a , and R 3a , is independently hydrogen, methyl, methoxy, --NHCOCH 3 or --NHCONH 2 ; and each R 2 and R 4 is preferably R 2a and R 4a where each R 2a and R 4a is independently hydrogen, methyl or methoxy. More preferably each R 1 and R 3 is R 1b and R 3b , where R 1b and R 3b is independently hydrogen, methyl or methoxy, and each R 2 and R 4 is hydrogen. Most preferably, each of R 1 to R 4 is hydrogen.
  • the floating sulphonic acid group in both naphthyl rings is preferably in the 3-position.
  • Each of X 1 to X 7 defined as an amino group is preferably a radical ##STR5## in which R 5 is hydrogen or C 1-4 alkyl,
  • Q is C 2-6 alkylene, C 3-6 alkylene substituted by one or two hydroxy groups, or C 4-6 alkylene which is interrupted by --0--, --S-- or --N(R 5 ) --, and
  • Z is --NR 6 R 7 or -- ⁇ NR 8 R 9 R 10 in which
  • each R 6 and R 7 is independently hydrogen; C 1-6 alkyl; C 2-6 alkyl monosubstituted by hydroxy, C 1-4 alkoxy or cyano; phenyl; phenyl substituted by one to three substituents selected from halogen, C 1-4 alkyl and C 1-4 alkoxy; phenyl(C 1-4 alkyl); phenyl(C 1-4 alkyl) the phenyl ring of which is substituted by one to three substituents selected from halogen, C 1-4 alkyl and C 1-4 alkoxy; C 5-6 cycloalkyl or C 5-6 cycloalkyl substituted by one to three C 1-4 alkyl groups; or
  • R 7 forms a pyrrolidine- , piperidine- or morpholine ring or a ring ##STR6## in which R 11 is hydrogen, C 1-4 alkyl or C 2-4 alkyl monosubstituted by hydroxy or amino, each R 8 and R 9 is independently C 1-6 alkyl; C 2-6 alkyl monosubstituted by hydroxy, C 1-4 alkoxy or cyano; phenyl; phenyl substituted by one to three substituents selected from halogen, C 1-4 alkyl and C 1-4 alkoxy; phenyl(C 1-4 alkyl); phenyl(C 1-4 alkyl) the phenyl ring of which is substituted by one to three substituents selected from halogen, C 1-4 alkyl and C 1-4 alkoxy; C 5-6 cycloalkyl or C 5-6 cycloalkyl substituted by one to three C 1-4 alkyl groups, and R 10 is C 1-4 alkyl or
  • R 10 forms a ring ##STR7## in which U is --CH 2 --, --0-- or --N(R 11 )--, or a pyridinium group which is unsubstituted or substituted by one or two methyl groups,
  • each -- ⁇ NR 8 R 9 R 10 is independently balanced by the negative charge of SO 3 ⁇ in the compounds of formula I to form an internal salt or by An ⁇ which is an external non-chromophoric anion, and
  • R 12 is C 2-4 alkyl monosubstituted by amino or hydroxy.
  • any halogen is preferably fluorine, chlorine or bromine, more preferably, it is chlorine or bromine, and especially chlorine.
  • any alkyl or alkylene group present is linear or branched unless indicated otherwise.
  • the hydroxy or alkoxy group is preferably bound to a carbon atom which is not directly bound to this nitrogen atom. If any alkylene group is substituted by two hydroxy groups, these hydroxy groups are preferably bound to different carbon atoms which in addition are preferably not adjacent carbon atoms.
  • any alkylene chain interrupted by --O--, --S-- or --N(R 5 )-- which is bound to a nitrogen atom preferably --O--, --S-- or --N(R 5 ) -- is bound to a carbon atom which is not directly attached to this nitrogen atom.
  • R 5 is preferably R 5a , where R 5 , is hydrogen or methyl.
  • Any linear alkylene as Q is preferably --(CH 2 ) n -- in which n is 2 or 3; any hydroxy-substituted alkylene as Q is preferably ##STR8##
  • Any branched alkylene as Q is preferably ##STR9## in which the marked carbon atom is attached to --N(R 5 ) --.
  • the alkylene group is interrupted by a hetero atom, it is preferably --(CH 2 ) n --Y--(CH 2 ) n -- in which n is 2 or 3 and Y is --O-- or --N(R 5a )--.
  • Q is preferably Q a , where Q a is C 2-4 alkylene, monohydroxy-substituted C 3-4 alkylene or --(CH 2 ) n --Y--(CH 2 ) n --; more preferably Q b , where Q b is ##STR10## or -(CH 2 ) 2 --NH--(CH 2 ) 2 --; most preferably it is Q c , where Q c is --(CH 2 ) n -- or ##STR11## in which n and Y are as defined above, and each marked carbon atom is bound to --N(R 5 ) --.
  • R 6 and R 7 are preferably R 6a and R 7a where each R 6a and R 7a is independently hydrogen, C 1-4 alkyl, C 2-3 hydroxyalkyl or benzyl, or --NR 6a R 7a is piperidino, morpholino or ##STR12## in which R 11a is hydrogen, methyl, 2-hydroxyethyl or 2-aminoethyl.
  • R 6b and R 7b are R 6b and R 7b , where R 6b and R 7b are the same and are hydrogen, methyl, ethyl or 2-hydroxyethyl, or --NR 6b R 7b is piperidino, morpholino or ##STR13##
  • R 6 and R 7 are R 6c and R 7c , where R 6c and R 7c are the same and are hydrogen, methyl or ethyl.
  • R 8 and R 9 are preferably R 8a and R 9a , where each R 5a and R 9a is methyl or ethyl, preferably R 8a and R 9a are the same;
  • R 10 is preferably R 10a , where R 10a is methyl, ethyl or benzyl; or -- ⁇ NR 8a R 9a R 10a is a pyridinium group which is unsubstituted or substituted by one or two methyl groups.
  • Z is preferably Z a , where Z a is --NR 8a R 7a or -- ⁇ NR 8a R 9a R 10a ; more preferably, it is Z b , where Z b is --NR 6b R 7b or -- ⁇ NR 8a R 9a R 10a ; most preferably it is Z c , where Z c is --NR 6c R 7c .
  • X 1 to X 4 are preferably X 1a to X 4a , where each of X 1a to X 4a , is independently ##STR14## more preferably they are X 1b to X 4b , where each of X 1b to X 4b is independently --NH--Q b --Z b or ##STR15## even more preferably they are X 1c to X 4c , where each of X 1c to X 4c is independently --NH--Q c Z c or ##STR16##
  • X 1 to X 4 are X 1d to X 4d , where each of X 1d to X 4d is independently --NH--(CH 2 ) n --NR 6d R 7d , ##STR17## in which n is 2 or 3 and R 6d and R 7d are methyl or ethyl and are the same.
  • X 5 is preferably X 5a , where X 5a is ##STR18## or more preferably, it is X 5b , where X 5b is --NH--(CH 2 ) n Z b ' in which n is 2 or 3 and Z b ' has one of the significances of Z b but independent thereof, with the exception of --NH 2 ; most preferably, X 5 is X 5c , where X 5c is --NH--(CH 2 ) n --NR 6d R 7d wherein n, R 6d and R 7d are as defined above.
  • Preferred compounds of formula I correspond to formula Ia, ##STR19## in which R 1b , R 3b and X 1b to X 5b are as defined above, with the proviso that at least two of X 1b to X 4b are independently ##STR20##
  • X 1b to X 4b are X 1c to X 4c , with the proviso that at least two of X 1c to X 4c are independently ##STR21##
  • (2) X 1b to X 4b are X 1d to X 4d , with the proviso that at least two of X 1d to X 4d are independently ##STR22##
  • X 5b is X 5c ; (5) those of (1) to (4) in which R 1b and R 3b are both hydrogen.
  • preferred compounds of formula I and Ia are symmetrical, i.e. the two monoazo radicals connected by the triazinylamino bridge are identical.
  • an external anion An ⁇ is present to balance the positive charge of a quaternary ammonium ion defined for X 1 to X 5 , it can be any non-chromophoric organic or inorganic anions such as those conventional in the field of basic dyestuff chemistry. Suitable anions include chloride, bromide, lactate, acetate, propionate, citrate, oxalate, malate, maleate, succinate, methyl sulphate, ethyl sulphate and hydrogen sulphate.
  • the sulphonic acid groups of the compounds of formula I are normally ionised and are present as SO 3 ⁇ . They form either internal salts with the basic amino groups or cationic ammonium groups X 1 to X 5 , or external salts under alkaline conditions. Suitable external cations to balance the negative charge of SO 3 ⁇ are any non-chromophoric cations such as alkali metal ions, e.g. of lithium, sodium and potassium, or any unsubstituted or substituted ammonium ions.
  • Suitable acids are dilute mineral acids such as hydrochloric acid, sulphuric acid and phosphoric acid, or preferably organic acids such as formic acid, acetic acid, methoxy acetic acid, lactic acid, citric acid, glycolic acid and methane sulphonic acid.
  • the compounds of formula I according to the invention can be prepared by reacting a compound of formula II ##STR24## with an amine of formula X 5 --H in which R 1 to R 4 and X 1 to X 5 are as defined above.
  • Those compounds of formula I in which X 1 is identical to X 3 and X 2 is identical to X 4 and the floating sulphonic acid group in the naphthyl radicals is either in the 3- or in the 4-position, may be prepared by diazotising one mole of a compound of formula III ##STR25## on both sides and reacting with at least two moles of a compound of formula IV ##STR26## in which R 1 to R 4 , X 1 , X 2 and X 5 are as defined above.
  • Condensation of a compound of formula II with an amine X 5 --H is suitably carried out at a temperature of about 95° C.
  • Diazotisation of a compound of formula III and also the coupling reaction with a compound of formula IV can be carried out according to known methods; coupling is preferably effected at a pH of 6 to 8.
  • the compounds of formula I may be isolated in accordance with conventional methods, for example by precipitating the compound of formula I from the reaction solution, filtering off and drying. By the addition of an appropriate acid, the resultant compound of formula I can also be obtained in form of a solution which is ready to use.
  • the starting compounds of formulae II, III and IV and also the amines X 5 --H are either known or may be prepared in accordance with known methods using known starting materials, i.e. by corresponding condensation and coupling reactions, starting with cyanuric chloride in which the stepwise exchange of the chlorine atoms on the triazine ring is effected in a manner known per se and takes place under conditions which are conventional for the exchange of the first (at a temperature of about 0° to 5° C.), second (at a temperature of about 40° to 60° C.) and third (at a temperature of about 95° C.) chlorine atom on the triazine ring.
  • the compounds of formula I in form of their internal/acid addition or quaternary ammonium salts can be used as dyestuffs for dyeing or printing cationically dyeable materials such as single or mixed polymers of acrylonitrile, acid-modified polyester fibres; leather, cotton, bast fibres such as hemp, flax, sisal, jute, coir fibres and straw; regenerated cellulose fibres, glass fibres and paper.
  • the compounds according to the invention are preferably used for dyeing or printing hydroxy group- or nitrogen-containing organic substrates.
  • they can be used for dyeing or printing fibres, filaments or textiles produced therefrom which comprise natural or synthetic polyamide or natural or regenerated cellulose material, e.g., cotton, according to known methods.
  • Cotton is preferably dyed by the conventional exhaust process, for example from a long or short liquor and at room temperature to boiling temperature. Printing is effected by impregnation with a printing paste which is prepared by known methods.
  • the new compounds can also be employed for dyeing or printing leather, preferably chrome-tanned types of leather, by known methods.
  • inks may be used in the production of inks according to known methods.
  • the compounds of formula I are especially suited for dyeing or printing paper, e.g. for the production of mass-dyed, sized or unsized paper. They can also be used for dyeing paper by the dipping process or in the sizing press. Dyeing and printing take place by known methods.
  • the compounds of formula I may also be used in the form of dyeing preparations. This form of application is preferred in particular when dyeing paper.
  • the processing into stable liquid, preferably aqueous, concentrated dyeing preparations may be effected in accordance with known methods, advantageously by dissolving in suitable solvents, optionally in the presence of an adjuvant, e.g. a hydrotropic compound or a stabiliser.
  • an adjuvant e.g. a hydrotropic compound or a stabiliser.
  • a suitable composition of a liquid preparation is as follows (parts are by weight):
  • a solubilising agent for example glycols such as ethylene glycol, propylene glycol, diethylene glycol, tri-ethylene glycol and hexylene glycol; glycol ethers such as methyl cellosolve, methyl carbitol and butyl polyglycol; urea; formamide and dimethylformamide.
  • a solubilising agent for example glycols such as ethylene glycol, propylene glycol, diethylene glycol, tri-ethylene glycol and hexylene glycol; glycol ethers such as methyl cellosolve, methyl carbitol and butyl polyglycol; urea; formamide and dimethylformamide.
  • liquid aqueous dye preparations are stable and can be stored for a long time.
  • the compounds of formula I (in appropriate salt form) have good solubility properties, and are especially notable for their good solubility in cold water. Due to their high substantivity, the dyestuffs are absorbed practically quantitatively and show good build-up. When producing sized and unsized paper, the waste water is practically colourless or is only slightly coloured.
  • the dyestuffs can be added to the paper pulp directly, i.e. without pre-dissolving, as a dry powder or in granules, without any reduction in brilliance or colour yield. When compared with unsized paper dyeings, the sized paper dyeings show no loss of depth.
  • the compounds of formula I can also be used for dyeing in soft water where the full colour yield is obtained. They do not mottle when dyed on paper, they are not inclined to produce two-sided effects on paper and are substantially insensitive towards fillers and pH variations.
  • the dyeings on paper exhibit good light fastness; after a long-term exposure to light, the shade alters tone-in-tone.
  • the dyed papers have a high level of fastness to bleeding. They show very good wet fastness properties not only to water, but also to milk, fruit juices, sweetened mineral water, soap water, tonic water, sodium chloride solution, and urine. In addition, they have good alcohol fastness. Paper which has been dyed with the compounds of formula I can be bleached both by oxidation and by reduction, which is important for the re-use of waste paper.
  • Fibrous materials containing mechanical wood pulp are dyed with the compounds according to the invention in a good and even quality.
  • the compounds of formula I are suitable for dyeing in combination.
  • the dyeings which are obtained when compounds of formula I are used together with dyestuffs which exhibit comparable dyeing properties, have good fastness properties.
  • the blue dyestuff which is formed precipitates and is filtered off. After drying, 60 parts of the dyestuff of formula (1c) ##STR29## are obtained which are stirred into 890 parts of demineralised water with the addition of 50 parts by volume of formic acid. A dye solution is obtained which is stable and ready to use which dyes paper a reddish blue shade. The waste water resulting from the dyeing is practically colourless. The wet- and light-fastness properties of the resultant paper dyeings are excellent.
  • the compound of formula (1b) can be prepared as follows:
  • the paper dyeings obtained with the dyes of Examples 2 to 12 are reddish blue and show good light- and wet-fastness properties.
  • the dyestuff thus obtained has the formula (13c) ##STR34## and dyes paper a reddish blue shade. These paper dyeings show good light- and wet-fastness properties.
  • the paper dyeings obtained with the compounds of Examples 14 to 23 show a blue shade and have good fastness properties.
  • the dyestuff is well soluble in water when an acid, such as formic acid, acetic acid or lactic acid, is present, and dyes paper a reddish blue shade. These paper dyeings are perfect with respect to back-water colouration and wet fastness properties.
  • the compound of formula (24a) can be prepared as follows:
  • the dyestuffs of Examples 2 to 24 can also be converted into liquid stable and ready to use dye solutions when adding the appropriate amount of water and formic acid to each dyestuff.
  • any other organic acid such as lactic-, acetic- and methoxy acetic-acid or a mixture thereof including formic acid, can be used to form an acid addition salt of each dyestuff which is well soluble in water.
  • Example 1 0.3 Part of the dyestuff powder of Example 1 (in acid addition salt form) is dissolved in 100 parts of hot water and cooled to room temperature. The solution is added to 100 parts of chemically bleached sulphite cellulose which have been ground in a hollander in 2000 parts of water. After thorough mixing for 15 minutes, sizing takes place in the usual way with rosin size and aluminium sulphate. Paper which is produced from this material has a reddish blue shade and exhibits good properties with respect to waste water colouration as well as light- and wet fastnesses.
  • Example 1 0.3 part of the dyestuff of Example 1 (as acid addition salt) or 3 parts of the liquid dye preparation according to Example 1,
  • the excess dye liquor is squeezed out through two rollers.
  • the dried length of paper is dyed reddish blue.
  • the dyestuffs of Examples 2 to 24 or a liquid-aqueous dyeing preparation thereof may be used to dye paper in accordance with the method described in Application Examples A to C.
  • the paper dyeings thus obtained have a blue shade and show good general fastness properties.
  • the dyestuffs of Examples 2 to 24 may be employed to dye cotton in accordance with the method described in Application Example D.
  • 100 Parts of freshly tanned and neutralised chrome grain leather are drummed for 30 minutes in a vat containing a dye liquor of 250 parts of water at 55° and 0.5 part of the dyestuff of Example 1 in acid addition salt form, and are treated in the same bath for a further 30 minutes with 2 parts of an anionic fat liquor based on sulphonated train oil.
  • the leathers are dried and finished in the usual way. An evenly dyed leather in a reddish blue shade is obtained.
  • the dyestuffs of Examples 2 to 24 can be used to dye leather in accordance with the above method.
  • vegetable-retanned leathers may similarly be dyed according to known methods.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
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US08/363,672 1992-05-13 1994-12-22 Basic disazo compounds containing sulphonic acid groups Expired - Lifetime US5498701A (en)

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JP (1) JP3902672B2 (de)
CH (1) CH684948A5 (de)
FR (1) FR2691157B1 (de)
GB (1) GB2266893B (de)
HK (1) HK1007157A1 (de)
IT (1) IT1261480B (de)
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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6130319A (en) * 1996-07-24 2000-10-10 Lexmark International, Inc. Methods of making cationic azo dye compounds having flocculating properties using reactive dyes
US20030148179A1 (en) * 2000-06-05 2003-08-07 Takao Uyama Sealing material for electrochemical element and electrochemical element containing the same
US20040158049A1 (en) * 2001-06-01 2004-08-12 Friedrich Lehr Basic mono-and bisazo compounds
US20060194803A1 (en) * 2002-02-05 2006-08-31 Hideki Kubota 2,4,6-Triamino-1,3,5-triazine derivative
CN1328324C (zh) * 2004-03-10 2007-07-25 杭州近江化工染料有限公司 一种高浓度液状阳离子染料的制备方法
US20090269553A1 (en) * 2006-04-07 2009-10-29 Clariant Finance (Bvi) Limited Acid dyes
US20100233443A1 (en) * 2006-06-25 2010-09-16 Clariant Finance (Bvi) Limited Acid dyes

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US6123763A (en) * 1997-12-22 2000-09-26 Toyo Ink Mfg. Co., Ltd. Pigment dispersing agent and pigment composition containing the same
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US6130319A (en) * 1996-07-24 2000-10-10 Lexmark International, Inc. Methods of making cationic azo dye compounds having flocculating properties using reactive dyes
US20030148179A1 (en) * 2000-06-05 2003-08-07 Takao Uyama Sealing material for electrochemical element and electrochemical element containing the same
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US7183409B2 (en) * 2001-06-01 2007-02-27 Clariant Finance (Bvi) Limited Basic mono- and bisazo compounds
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US7375222B2 (en) 2002-02-05 2008-05-20 Astellas Pharma Inc. 2,4,6-Triamino-1,3,5-triazine derivative
CN1328324C (zh) * 2004-03-10 2007-07-25 杭州近江化工染料有限公司 一种高浓度液状阳离子染料的制备方法
US20090269553A1 (en) * 2006-04-07 2009-10-29 Clariant Finance (Bvi) Limited Acid dyes
US8137416B2 (en) 2006-04-07 2012-03-20 Clariant Finance (Bvi) Limited Acid dyes
US20100233443A1 (en) * 2006-06-25 2010-09-16 Clariant Finance (Bvi) Limited Acid dyes
US7927384B2 (en) 2006-06-25 2011-04-19 Clariant Finance (Bvi) Limited Acid dyes

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ITRM930300A1 (it) 1994-11-10
JPH06157929A (ja) 1994-06-07
HK1007157A1 (en) 1999-04-01
CH684948A5 (de) 1995-02-15
JP3902672B2 (ja) 2007-04-11
SE511889C2 (sv) 1999-12-13
SE9301627D0 (sv) 1993-05-12
GB2266893B (en) 1995-06-21
FR2691157B1 (fr) 1997-06-06
GB9309544D0 (en) 1993-06-23
SE9301627L (sv) 1993-11-14
GB2266893A (en) 1993-11-17
ITRM930300A0 (it) 1993-05-10
FR2691157A1 (fr) 1993-11-19
IT1261480B (it) 1996-05-23

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